Asperanstinoids A–E: Undescribed 3, 5-dimethylorsellinic acid-based meroterpenoids from Aspergillus calidoustus. (October 2021)

• Record Type: Journal Article
• Authors: Mo, Shuyuan; Yin, Jie; Ye, Zi; Li, Fengli; Lin, Shuang; Zhang, Sitian; Yang, Beiye; Yao, Jun; Wang, Jianping; Hu, Zhengxi; Zhang, Yonghui
• Is Part Of: Phytochemistry. Volume 190(2021)
• Publication Date: 2021-10
• Subjects: Aspergillus calidoustus -- Trichocomaceae -- Meroterpenoids -- Cytotoxicity; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2021.112892
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Large-scale culture is a complementary and practical method for genome mining and OSMAC approaches to discover novel natural products through accumulation and reprocessing effects. By employing a large-scale culture approach, twelve 3, 5-dimethylorsellinic acid (DMOA)-based meroterpenoids, including five undescribed compounds, namely asperanstinoids A–E, were obtained from fungus Aspergillus calidoustus, which was isolated from the wetland soil collected at Dianchi Lake, Yunnan Province. The structures and absolute configurations of asperanstinoids A–E were determined by various spectroscopic analyses, including NMR spectroscopy, high-resolution electrospray ionization mass spectrometry (HRESIMS), single-crystal X-ray diffraction, and electronic circular dichroism (ECD) calculations, and the absolute configurations of three known compounds, dehydroaustinol, austinol, and austin, were confirmed via single-crystal X-ray diffraction for the first time. Notably, asperanstinoid A represents the second example of a DMOA-based meroterpenoid featuring a unique 6/5/6/6/6/5-fused hexacyclic skeleton with a rare "1, 13-epoxy" moiety. The cytotoxicity assay of all these isolates revealed that asperanstinoid D, dehydroaustinol, and austin displayed considerable cytotoxicity against the HL-60 and SU-DHL-4 tumor cell lines with IC50 values ranging from 15.7 to 27.8 μ M. Graphical abstract: Image 1 Highlights: Five undescribed meroterpenoids were characterized from Aspergillus calidoustus. Their structures were defined by NMR analyses, ECD calculations, and X-ray crystallography. Asperanstinoid A possesses a rare 6/5/6/6/6/5-fused ring system with a "1, 13-epoxy" moiety. Asperanstinoid D, dehydroaustinol, and austin displayed considerable cytotoxicity.